Cheap Flights from MDW to SJC

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The Cheapest Round-trip Tickets from to San Jose

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29 April 20264 May 2026DirectSouthwest AirlinesRT from 269

The Cheapest Flights for this Month from to San Jose

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23 March 202626 March 2026DirectSouthwest AirlinesRT from 1 212
26 March 202630 March 2026DirectSouthwest AirlinesRT from 992
27 March 202630 March 2026DirectSouthwest AirlinesRT from 688
28 March 202614 April 2026DirectSouthwest AirlinesRT from 886
30 March 20263 April 2026DirectSouthwest AirlinesRT from 792
31 March 20263 April 2026DirectSouthwest AirlinesRT from 728
1 April 20264 April 2026DirectSouthwest AirlinesRT from 770
2 April 20266 April 2026DirectSouthwest AirlinesRT from 676
3 April 20266 April 2026DirectSouthwest AirlinesRT from 679
4 April 20266 April 2026DirectSouthwest AirlinesRT from 650
9 April 202610 April 2026DirectSouthwest AirlinesRT from 569
10 April 202611 April 2026DirectSouthwest AirlinesRT from 546
14 April 202624 April 2026DirectSouthwest AirlinesRT from 444
26 April 202629 April 2026DirectSouthwest AirlinesRT from 389
27 April 20261 May 2026DirectSouthwest AirlinesRT from 282
28 April 202629 April 2026DirectSouthwest AirlinesRT from 284
29 April 20264 May 2026DirectSouthwest AirlinesRT from 269
2 May 20269 May 2026DirectSouthwest AirlinesRT from 366
4 May 20269 May 2026DirectSouthwest AirlinesRT from 358
22 May 202624 May 2026DirectSouthwest AirlinesRT from 433

The Cheapest Flights from to San Jose for the Year Ahead

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27 March 202630 March 2026DirectSouthwest AirlinesRT from 688
29 April 20264 May 2026DirectSouthwest AirlinesRT from 269
4 May 20269 May 2026DirectSouthwest AirlinesRT from 358
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